N-benzyl-4-chlorobenzenecarboximidamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4-chlorobenzenecarboximidamide
• 英文别名: N-benzyl-4-chlorobenzimidamide；N'-benzyl-4-chlorobenzenecarboximidamide
• 化学式: C₁₄H₁₃ClN₂
• 分子量: 244.724
• InChiKey: UXJDEKUGJUQMDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-chlorobenzenecarboximidamide 在 氧气 、 copper(l) chloride 作用下， 以 二甲基亚砜 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以75%的产率得到2,4-bis(4-chlorophenyl)-6-phenyl-1,3,5-triazine
  参考文献：
  名称：

  A novel straightforward synthesis of 2,4,6-triaryl-1,3,5-triazines via copper-catalyzed cyclization of N-benzylbenzamidines

  摘要：

  DOI：

  10.1016/j.tetlet.2014.10.091
• 作为产物：
  描述：

  对氯苯甲腈 在 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 N-benzyl-4-chlorobenzenecarboximidamide
  参考文献：
  名称：

  Orally Efficacious NR2B-Selective NMDA Receptor Antagonists

  摘要：

  A novel series of benzamidines as synthesized and shogun to exhibit NR2B-subtype selective NMDA antagonist activity. Compound 31 is orally active in a carrageenan-induced rat hyperalgesia model of pain and shows no motor coordination side effects. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01061-2

文献信息

• Guanidine Synthesis: Use of Amidines as Guanylating Agents
  作者：Mattijs Baeten、Bert U. W. Maes

  DOI：10.1002/adsc.201501146

  日期：2016.3.3

  hindered, oxidation‐sensitive and chiral amines. Examples for the synthesis of both acyclic and cyclic guanidines are provided. 2‐Propoxyphenyl iodide (2‐PrOPhI) by‐product, generated from the oxidant [N‐(p‐toluenesulfonyl)imino](2‐propoxyphenyl)iodinane (2‐PrOPhINTs), can be isolated in high yields making regeneration of the hypervalent iodine reagent possible. The utility and greenness of the synthetic

  据报道of可用于胍的串联或一锅合成。胍是通过将易得的稳定stable稳定氧化成碳二亚胺，然后与胺进行原位反应而获得的。该方案可以在绿色溶剂（碳酸二甲酯）中，在温和的反应条件下（30°C）执行。胺的范围很广，包括位阻胺，对氧化敏感的胺和手性胺。提供了合成无环和环状胍的实例。由氧化剂[ N-（p可以高产率地分离出[甲苯磺酰基]亚氨基]（2-丙氧基苯基）碘烷（2-PrOPhINTs），从而使高价碘试剂的再生成为可能。合成方法与最新技术相比，其实用性和绿色性通过抗高血压药物Pinacidil的新途径得以证明。新路线的过程质量强度（PMI）仅是经典路线的24％。
• Synthesis of Secondary Amides from<i>N</i>-Substituted Amidines by Tandem Oxidative Rearrangement and Isocyanate Elimination
  作者：Pradip Debnath、Mattijs Baeten、Nicolas Lefèvre、Stijn Van Daele、Bert U. W. Maes

  DOI：10.1002/adsc.201400648

  日期：2015.1.12

  The periodinane reagents are obtained from the commercially available phenyliodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N‐substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting

  在这项工作中，已经描述了将N-取代的idine转化为仲酰胺的有效串联过程。该过程涉及Ñ通过与双衬底的反应-acylurea形成（酰氧基）（苯基）-λ 3 -iodane随后的异氰酸酯的消除。通过与羧酸的配体交换从可商购的二乙酸苯基碘（III）苯乙酸[PhI（OAc）2（PIDA）]获得高碘烷试剂。该ñ预取代的idine底物很容易从容易获得的腈中合成。该方法适用于基于脂族和（杂）芳族胺的仲酰胺合成，包括由位阻酸和胺组成的挑战性酰胺。而且，该方案允许将目标酰胺（基于苯胺）中的空间体积与电子缺乏结合起来。基于涉及羧酸和胺的经典缩合反应，这样的化合物难以有效地合成。总体而言，在脂肪族和（杂）芳族体系中，合成方案都能将腈转化为仲酰胺。
• Chemoselective synthesis of 5,4′-imidazolinyl spirobarbiturates <i>via</i> NBS-promoted cyclization of unsaturated barbiturates and amidines
  作者：Hui Xu、Rong-Lu Huang、Zhu Shu、Ran Hong、Ze Zhang

  DOI：10.1039/d1ob00508a

  日期：——

  A selective cyclization of unsaturated barbiturates and amidines promoted by N-bromosuccinimide has been successfully developed to afford a vast variety of 5,4′-imidazolinyl spirobarbiturates in moderate to good yields. The present protocol features broad substrate scope, facile work-up procedure and mild reaction conditions, providing a novel strategy for the highly selective and efficient construction

  由N-溴代琥珀酰亚胺促进的不饱和巴比妥酸盐和脒的选择性环化已成功开发，以中等至良好的收率提供种类繁多的 5,4'-咪唑啉螺巴比妥酸盐。本协议具有广泛的底物范围、简便的后处理程序和温和的反应条件，为结构多样的螺咪唑啉的高选择性和高效构建提供了一种新策略。
• Base-promoted formal [4 + 1+1] annulation of aldehyde, N -benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines
  作者：Jin Yuan、Jingbo Li、Bingbing Wang、Song Sun、Jiang Cheng

  DOI：10.1016/j.tetlet.2017.11.020

  日期：2017.12

  A base-promoted formal [4 + 1+1] annulation of aldehyde, N-benzyl amidine and DMSO was developed, leading to a series of 2,4,6-triaryl pyrimidines in moderate to good yields. Notably, DMSO served as a methine source, which was activated by base rather than either Lewis acid or electrophile. Molecular O-2 was the sole eco-friendly oxidant during this procedure. (C) 2017 Published by Elsevier Ltd.
• Orally Efficacious NR2B-Selective NMDA Receptor Antagonists
  作者：Christopher F Claiborne、John A McCauley、Brian E Libby、Neil R Curtis、Helen J Diggle、Janusz J Kulagowski、Stuart R Michelson、Kenneth D Anderson、David A Claremon、Roger M Freidinger、Rodney A Bednar、Scott D Mosser、Stanley L Gaul、Thomas M Connolly、Cindra L Condra、Bohumil Bednar、Gary L Stump、Joseph J Lynch、Alison Macaulay、Keith A Wafford、Kenneth S Koblan、Nigel J Liverton

  DOI：10.1016/s0960-894x(02)01061-2

  日期：2003.2

  A novel series of benzamidines as synthesized and shogun to exhibit NR2B-subtype selective NMDA antagonist activity. Compound 31 is orally active in a carrageenan-induced rat hyperalgesia model of pain and shows no motor coordination side effects. (C) 2003 Elsevier Science Ltd. All rights reserved.